Upperville VA Real Estate & Homes for Sale

Gorgeous mountain views and ultimate privacy await you at this beautifully remodeled farmhouse-style retreat. Nestled on 10 peaceful, wooded acres, this home offers a serene escape while remaining just minutes from Sky Meadows State Park, local breweries, and vineyards. Currently operating as a successful Airbnb, the property presents a flexible opportunity-whether you're seeking a private getaway, an income-producing investment, or a home designed for entertaining. With no HOA and surrounded by mature trees, you'll enjoy both seclusion and freedom. The location is ideal, situated just 2.5 miles from the Upperville Colt & Horse Show and 4.5 miles from the Middleburg Classic, with easy access to Middleburg, Delaplane, Bluemont, and major highways. Inside, the open-concept layout invites you into a stunning kitchen outfitted with granite countertops, stainless steel appliances, a spacious island, and a double oven-perfect for cooking and entertaining with ease. Two expansive owners suites, each with its own private en-suite bath, offer luxurious comfort and flexibility. A charming built-in shelving unit paired with a bay window creates a cozy space to relax and take in the views. The screened-in porch, complete with a stone fireplace, allows you to enjoy the beauty of every season in comfort. With four bedrooms, four and a half bathrooms, and a layout designed for entertaining both indoors and out, this home offers the perfect blend of modern amenities and rustic charm. Completely updated and equipped with HughesNet internet, staying connected is never an issue. The home can be sold fully furnished for an additional cost, making it truly turnkey. This is a rare gem in Virginia horse and wine country-dont miss your chance to own a slice of paradise.

Take a step back in time and own a piece of history. â??The Armistead Houseâ?? is a charming, historic brick home in the heart of Upperville, Virginia. Designated a Virginia Historic Landmark and on the National Register of Historic Places, it was built in 1823 by a doctor whose medical oï¬?ce was the small stone structure known today as the Upperville Library. Mr. Bowles Armistead purchased the home before the Civil War and since that time the Armistead House has been in their family for almost two centuries. In this first time oï¬?ering, you will have the opportunity to own a piece of history in the heart of beautiful Piedmont hunt country. The original 1823 colonial brick structure was enhanced in 1923 with an addition mirroring the original building. A first floor master addition was added in the 1970s. Enter the handsome front door of this beautiful brick home with dark green plantation shutters and original wavy glass windows to the foyer of the home, complete with ten foot ceilings, a coat closet and the original wood plank flooring with historic square cut nails. To the left of the foyer is a formal living room with a wood burning fireplace and to the right is the formal dining room with fireplace. All three rooms have doors leading out to a charming covered porch overlooking the yard with mature trees, boxwoods, peonies, and a stone retaining garden. The side door to the house is next to your private parking area which leads to the 1970's added mudroom/laundry room. There are multiple closet spaces and built-in bookshelves in the hallway for ample storage. There you will also find a first floor master bedroom with attached full bath. The galley style kitchen to the left has beautiful natural lighting with charming latch windows. Two additional bedrooms are found upstairs. One with a hallway full bathroom and original closed fireplace and mantel and the other with two large closets and dressing room with full bathroom. The second floor has access to the upper level screened in porch overlooking the backyard. This house comes complete with a full generator. The Armistead House is situated in the heart of historic Upperville nestled in between two historic churches - Upperville Baptist and Trinity Episcopal Church. Walk to church, the library, post oï¬?ce or dinner at Hunters Head Pub or simply enjoy the evening on your covered porch overlooking the gardens and rolling countryside beyond. Minutes from Middleburg, Virginia and an easy commute to Washington, D.C. and the surrounding airports.

Opportunity to to own a charming historic church building in the heart of Upperville. A perfect location and opportunity to live in the heart of the historic village of Upperville just west of Middleburg. The church and the studio have been both renovated and connected to offer more living space and a seamless home in excellent condition. Beautiful Mountain views from the large back yard. Close to Sky Meadows State Park, the Appalachian Trail and many local Vineyards.